Film ozonolysis in a tubular or multitubular reactor

Abstract

The disclosure relates to a method of performing ozonolysis or ozone-based oxidation on a liquid or emulsified reagent using a tubular falling firm reactor with one or multiple tubes wherein the combined ozone and carrier gas flow is co-current.

What is claimed is: 
     
       1. A method of performing ozonolysis or ozone-based oxidation on a liquid or emulsified reagent using an industrial scale tubular falling film reactor with multiple tubes wherein the combined ozone and carrier gas flow is co-current, and wherein the ozonolysis occurs continuously without accumulation of large amounts of hazardous intermediates, and wherein the tubes are cooled by flow of a coolant;
 wherein the liquid or emulsified reagent comprises a compound selected from hydroxycitronellene, methoxycitronellene, a rose ketone, fatty acid methyl esters, triglycerides, fatty alcohols, fatty esters, diterpenes, sesquiterpenes, monoterpenes, allyl ethers, alpha olefins, rosin acids, tertiary amines, alkenes, alkynes, amides, carboxylic acids, and aromatic compounds, provided that said compound is susceptible to ozone oxidation. 
 
     
     
       2. The method of  claim 1 , wherein method comprises two or more industrial scale tubular falling film reactors with multiple tubes connected in series to process a continuous stream of the liquid or emulsified reagent. 
     
     
       3. The method of  claim 1 , wherein the carrier gas is selected from air, oxygen (O 2 ), and an oxygen (O 2 )/nitrogen (N 2 ) mixture. 
     
     
       4. The method of  claim 3 , wherein the carrier gas is air and the ozone concentration in the carrier gas is from 2.5% to 10%. 
     
     
       5. The method of  claim 1 , wherein the liquid or emulsified reagent is an emulsion in water. 
     
     
       6. The method of  claim 1 , wherein the reactor comprises the multiple tubes in parallel enclosed in a cylindrical reactor. 
     
     
       7. The method of  claim 1 , wherein the diameter of the tube(s) is between 5 mm and 30 mm. 
     
     
       8. The method of  claim 7 , wherein the diameter of the tube(s) is between 10 mm and 25 mm. 
     
     
       9. The method of  claim 1 , wherein the gas flow rate is from 10 to 1500 L/min in each of said tube or tubes. 
     
     
       10. The method of  claim 1 , wherein the gas flow rate is about 150 L/min in each of said tube or tubes. 
     
     
       11. The method of  claim 1 , wherein the tubes are between 1 and 7 meters in length or wherein the tubes are about 6 meters in length, or both. 
     
     
       12. A method of performing ozonolysis or ozone-based oxidation on a liquid or emulsified reagent using an industrial scale tubular falling film reactor with multiple tubes wherein the combined ozone and carrier gas flow is co-current, and wherein the ozonolysis occurs continuously without accumulation of large amounts of hazardous intermediates, and wherein the tubes are cooled by flow of a coolant, wherein the liquid or emulsified reagent comprises a fatty acid susceptible to ozone oxidation, wherein the carrier gas is air and the ozone concentration in the carrier gas is from 2.5% to 10%. 
     
     
       13. The method of  claim 1 , wherein the liquid or emulsified reagent comprises a compound selected from hydroxycitronellene, methoxycitronellene, fatty acid methyl esters, fatty alcohols, diterpenes, sesquiterpenes, and monoterpenes, provided that said compound is susceptible to ozone oxidation. 
     
     
       14. The method of  claim 13 , wherein the liquid or emulsified reagent comprises hydroxycitronellene. 
     
     
       15. The method of  claim 13 , wherein the liquid or emulsified reagent comprises methoxycitronellene. 
     
     
       16. The method of  claim 13 , wherein the liquid or emulsified reagent comprises a fatty acid methyl ester. 
     
     
       17. The method of  claim 13 , wherein the liquid or emulsified reagent comprises methyl oleate. 
     
     
       18. The method of  claim 13 , wherein the liquid or emulsified reagent comprises abietic acid or an ester thereof, pinene, limonene, ionone, or dihydromyrcenol. 
     
     
       19. The method of  claim 1 , wherein the product is selected from hydroxymelonal, methoxymelonal, methyl azealdehyde, nonanal, cyclocitral, or mixtures thereof. 
     
     
       20. The method of  claim 1 , wherein the product is hydroxymelonal. 
     
     
       21. The method of  claim 1 , wherein the product is methoxymelonal. 
     
     
       22. The method of  claim 1 , wherein the product is a mixture of methyl azealdehyde and nonanal. 
     
     
       23. The method of  claim 4 , wherein the carrier gas is air and the ozone concentration in the carrier gas is from 2.5% to 5%.